Water → HCID 18536711, compound

HRID 412071Notes

Reaction equation

HRID 412071 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([O:15][CH2:16][C:17]2[N:18]=[CH:19][N:20]([C:22]3[CH:23]=[C:24]4[C:29](=[CH:30][C:31]=3[C:32]([F:35])([F:34])[F:33])[NH:28][C:27](=[O:36])[C:26]([C:37]([O:39]CC)=[O:38])=[CH:25]4)[CH:21]=2)=[O:14])=[CH:8][CH:7]=1)=[O:5])C.[OH-].[Li+].O>C(O)C>[C:4]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([O:15][CH2:16][C:17]2[N:18]=[CH:19][N:20]([C:22]3[CH:23]=[C:24]4[C:29](=[CH:30][C:31]=3[C:32]([F:35])([F:33])[F:34])[NH:28][C:27](=[O:36])[C:26]([C:37]([OH:39])=[O:38])=[CH:25]4)[CH:21]=2)=[O:14])=[CH:8][CH:7]=1)([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 962Water2×HCID 3939Lithium Hydroxide2×HCID 9808166HCID 9808166, compound

Product 1

HCID 18536711HCID 18536711, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of the compound of Example 18 (1.13 g, 1.97 mmol) in ethanol (30 ml) was added 1 mol/L aqueous solution of lithium hydroxide (9.26 ml, 9.26 mmol) and successively water (15 ml), and, after stirring for 4 hours at room temperature, the mixture was allowed to stand statically overnight. After stirring for 16 hours at 30° C., ice water was added to the reaction mixture and the insolubles were filtered off. Then, the pH value was brought to 4 with 3 mol/L hydrochloric acid and solvent was distilled off. Water was added to the residue obtained, the precipitated crystals were collected by filtration, washed with water, and then dried under reduced pressure. After the powder obtained was suspended into water (40 ml), 1 mol/L aqueous solution of lithium hydroxide (9.26 ml, 9.26 mmol) was added and the mixture was stirred for 30 minutes at 50° C. Ice water was added to the reaction mixture, the insolubles were filtered off, then the pH value was brought to 4 with 3 mol/L hydrochloric acid, and solvent was distilled off. Water was added to the residue obtained, the precipitated crystals were collected by filtration, washed with water, and then dried under reduced pressure, thereby obtaining 757 mg of title compound as pale yellow powder.

Workup

  1. waitto stand statically overnight
  2. stirringAfter stirring for 16 hours at 30° C.
  3. filtrationthe insolubles were filtered off
  4. distillationwas distilled off
  5. additionWater was added to the residue
  6. customobtained
  7. filtrationthe precipitated crystals were collected by filtration
  8. washwashed with water
  9. customdried under reduced pressure
  10. customAfter the powder obtained
  11. additionwas added
  12. stirringthe mixture was stirred for 30 minutes at 50° C
  13. filtrationthe insolubles were filtered off
  14. distillationwas distilled off
  15. additionWater was added to the residue
  16. customobtained
  17. filtrationthe precipitated crystals were collected by filtration
  18. washwashed with water
  19. customdried under reduced pressure

Sources & evidence

ORD record
ord-9b7235fdbf8044478af862a9130d1fcb
Source dataset
uspto-grants-2003_05
Patent number
US06562839B1

Reaction notes

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